Sweet glycosides

Neohesperidin Semi-synthetic from flavanone glycoside Sweet (1000-1500X... 

Cyclocarioside A (46) is a dammarane-type triterpenoid glycoside sweet principle from the leaves of Cyclocarya paliurus (Batal.) Iljinsk (Juglandaceae), a plant used in the People s Republic of China in the treatment for diabetes [81]. Recently, another sweet-tasting principle, cyclocarioside I (47), was isolated from the same plant along with two other compounds with the same dammarane-type triterpenoid aglycone structure [82]. Cyclocarioside I was rated as about 250 times sweeter than sucrose [82]. 

Stevioside and rebaudioside A are diterpene glycosides. The sweetness is tainted with a bitter and undesirable aftertaste. The time—intensity profile is characteristic of naturally occurring sweeteners slow onset but lingering. The aglycone moiety, steviol [471 -80-7] (10), which is the principal metaboHte, has been reported to be mutagenic (79). Wide use of stevia ia Japan for over 20 years did not produce any known deleterious side effects. However, because no food additive petition has been presented to the FDA, stevioside and related materials caimot be used ia the United States. An import alert against stevia was issued by the FDA ia 1991. In 1995, however, the FDA revised this import alert to allow the importation and use of stevia as a diet supplement (80), but not as a sweetener or an ingredient for foods. Several comprehensive reviews of stevia are available (81,82). 

Sweetness is a quality that defies definition, but whose complexity can be appreciated merely by examining the molecular structures of those compounds that elicit the sensation. They come in all molecular shapes and sizes, and they belong to such seemingly unrelated classes of compounds as aliphatic and aromatic organic compounds, amino acids, peptides and proteins, carbohydrates, complex glycosides, and even certain inorganic salts. 

All of the mono-O-methylated hexopyranosides are sweet, with only a trace of bitterness. The bitterness is more pronounced in the methyl glycoside derivatives, and this was attributed to the presence of two lipophilic centers (—OMe) in the methyl glycosides and only one in the a,a-trehalose analogs. ... 

Table X), sweetness is not normally observed for ethyl glycosides, and does not occur at all for sugars having larger aglycons these are either bitter or very bitter. ...

Of this class of naturally occurring, sweet compounds, the flavanone glycosides found in citrus fruits have achieved considerable interest, owing to the systematic studies of Horowitz and Gentili " (see Fig. 20). 

Fig. 21.—Schematic Diagram of the Proposed Types of Bonding of Sweet Glycosides to the Taste-bud Receptor-sites. ...

It is known that the naturally occurring dihydrochalcone glycosides phloridzin (75) and glycyphillin (76), which are 2-yl glycosides, possess little or no sweetness, whereas phyllodulcin (77), which is not a glycoside, has the same taste properties as the dihydrochalcones it is 400 times sweeter than sucrose. ... 

It thus appears that the taste of the dihydrochalcones is not solely controlled by the sugar moiety, and subsequent studies 220 confirmed this. The flavanone 78 and the non-glycosidic dihydrochalcone 81 are intensely sweet. Furthermore, replacement of the bulky glycosyl residue by carboxyalkyl " (82) or sulfoalkyl (83) substituents did not significantly... 

The structure-sweetness relationships of other naturally occurring, sweet glycosides have received very little attention. In most cases, virtually no systematic, structural modifications have been reported. 

Bitter taste, like sweet taste, is exhibited by a very diverse group of chemical compounds. Because the bitter taste is generally regarded as unpleasant, and because it is often associated with such compounds as those alkaloids and glycosides that are harmful to man, detailed studies have been minimal. There is thus very little information available from which to deduce the chemical grouping common to those compounds eliciting the bitter response. 

Over 2,650 plant species can produce hydrogen cyanide (Seigler 1991 Swain et al. 1992). These include edible plants such as almonds, pits from stone fruits (e.g., apricots, peaches, plums, cherries), sorghum, cassava, soybeans, spinach, lima beans, sweet potatoes, maize, millet, sugarcane, and bamboo shoots (Fiksel et al. 1981). The cyanogenic glycoside content of a foodstuff is usually expressed as the amount of cyanide released by acid hydrolysis glycoside concentrations are rarely reported (WHO 1992). 

Coumarin glycosides are found throughout the plant kingdom (Burrows and Tyrl, 2001). Seeds of Aesculus glabra (Ohio buckeye) contain the coumarin esculin, which is a mild neurotoxin. Sweet clovers Melilotus spp.) contain coumarins that are considered harmless unless moldy conditions exist, in which fungal activity produces the double coumarin dicoumarol. Dicoumarol is a... 

Alkaline hydrolysis of the CHCls-soluble resin glycoside mixture from dry roots of sweet potato (Ipomoea batatas) afforded two glycosidic acids, simonic acids A (hexadecanoic acid, (115)-[(0-6-deoxy-a-L-mannopyranosyl-(1 3)-0-[6-deoxy-a-L-mannopyranosyl-(l—>4)]-0-6-deoxy-a-L-mannopyranosyl-(1 4)-0-6-deoxy-... 

Noda N, Horiuchi Y (2008) The Resin Glycosides from the Sweet Potato Ipomoea batatas L. Lam.). Chem Pharm Bull 56 1607... 

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